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Au(I)‐Catalyzed Annulation of Benzofurazan N‐oxides with Ynamides: From Predicting the Chemo‐Selectivity to the Synthesis of 7‐Nitroindole Derivatives
Chinese Journal of Chemistry ( IF 5.4 ) Pub Date : 2019-11-22 , DOI: 10.1002/cjoc.201900395
Changlei Zhu 1 , Luyao Kou 1 , Xiaoguang Bao 1
Affiliation  

It could be proposed that gold(I)‐catalyzed reactions of ynamides with benzofurazan N‐oxides might proceed through either O‐attack or N‐attack to afford α‐oxo or α‐imino Au(I)‐carbenoid intermediates. Computational studies were performed to predict that benzofurazan N‐oxides are ready to undergo the chemoselective N‐attack to the Au(I)‐activated ynamides to generate the α‐imino Au(I)‐carbenoid intermediate. Experimental studies were carried out to confirm the computational results and the 7‐nitroindole derivatives were synthesized in a concise and efficient manner. The unfavored O‐attack for benzofurazan N‐oxides, which is in contrast to nitrones and pyridine/quinoline N‐oxides, in the Au(I)‐catalyzed reactions with ynamides is rationalized.

中文翻译:

Au(I)催化的联呋喃氮氧化物与酰胺的环合:从预测化学选择性到合成7-硝基吲哚衍生物

可以建议,金(I)催化的酰胺与苯并呋喃山N-氧化物的反应可通过O攻击或N攻击进行,以提供α-氧代或α-亚氨基Au(I)-类胡萝卜素中间体。进行了计算研究,以预测苯并呋喃氮氧化物准备好对Au(I)活化的酰胺进行化学选择性N攻击,生成α-亚氨基Au(I)类胡萝卜素中间体。进行实验研究以确认计算结果,并且以简洁有效的方式合成了7-硝基吲哚衍生物。不利的O在Au(I)催化的与酰胺反应中,对苯并呋喃氮氧化物的攻击(与硝酮和吡啶/喹啉N氧化物相反)是合理的。
更新日期:2019-11-26
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